He has acted in three Wes Anderson films — with a main role in Bottle Rocket (1996) —and other notable credits include Rushmore (1998), The Royal Tenenbaums (2001), The Big Bounce (2004), Fever Pitch (2005), Idiocracy (2006), Church Ball (2006), Whip It! (2009), Druid Peak (2014), Hall Pass (2011), and Time Trap (2017).